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Showing metabocard for Perillyl aldehyde (HMDB0003647)

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enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 02:30:13 UTC
Update Date2023-02-21 17:16:46 UTC
HMDB IDHMDB0003647
Secondary Accession Numbers
  • HMDB0006315
  • HMDB03647
  • HMDB06315
Metabolite Identification
Common NamePerillyl aldehyde
DescriptionPerillyl aldehyde belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, perillyl aldehyde is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on Perillyl aldehyde.
Structure
Data?1676999806
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003647 (Perillyl aldehyde)

Perillyl aldehyde
  Mrv1652309042000302D          
  Marvin  09150600092D          
 12 12  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
  9  4  1  0  0  0  0
  7 11  2  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 12  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
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3D MOL for HMDB0003647 (Perillyl aldehyde)

HMDB0003647
     RDKit          3D
Perillyl aldehyde
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.4180   -1.4517    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -0.4553    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622    0.5582   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837   -0.2674   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -1.3030    0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -1.0445   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.1994   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    0.4172   -0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -0.5385   -0.8932 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598    1.3896    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    1.0840    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7484   -2.1925    1.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4728   -1.5665    0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7576    0.0561   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1992    1.2666    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059    1.1475   -1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562   -0.2613   -1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -2.3358    0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -1.1709    1.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890   -1.9048   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9713    1.4111   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552    2.1124   -0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    1.9121    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.8890   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295    1.0491    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
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3D SDF for HMDB0003647 (Perillyl aldehyde)

Perillyl aldehyde
  Mrv1652309042000302D          
  Marvin  09150600092D          
 12 12  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
  9  4  1  0  0  0  0
  7 11  2  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 12  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003647

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(=O)C1=CCC(CC1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3

> <INCHI_KEY>
RUMOYJJNUMEFDD-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.295884859075834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.2528889983333333

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.326978487493531

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.272099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-perillaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0003647 (Perillyl aldehyde)

HMDB0003647
     RDKit          3D
Perillyl aldehyde
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.4180   -1.4517    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -0.4553    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622    0.5582   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837   -0.2674   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -1.3030    0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -1.0445   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.1994   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    0.4172   -0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -0.5385   -0.8932 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598    1.3896    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    1.0840    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7484   -2.1925    1.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4728   -1.5665    0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7576    0.0561   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1992    1.2666    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059    1.1475   -1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562   -0.2613   -1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -2.3358    0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -1.1709    1.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890   -1.9048   -0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9713    1.4111   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552    2.1124   -0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    1.9121    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.8890   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295    1.0491    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
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PDB for HMDB0003647 (Perillyl aldehyde)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Perillyl aldehyde                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       1.334   3.850   0.000  0.00  0.00           H+0
CONECT    1   11    6    2                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    9    5    3                                                  
CONECT    5    6    4                                                       
CONECT    6    5    1                                                       
CONECT    7   11                                                            
CONECT    8    9                                                            
CONECT    9    4    8   10                                                  
CONECT   10    9                                                            
CONECT   11    1    7   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0003647 (Perillyl aldehyde)

COMPND    HMDB0003647
HETATM    1  C1  UNL     1      -2.418  -1.452   0.786  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.920  -0.455   0.092  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.862   0.558  -0.468  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.484  -0.267  -0.173  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.388  -1.303   0.462  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.773  -1.044  -0.014  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.179   0.199  -0.138  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.543   0.417  -0.608  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.328  -0.538  -0.893  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.360   1.390   0.163  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.077   1.084   0.426  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.748  -2.192   1.197  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.473  -1.566   0.965  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.758   0.056  -0.921  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.199   1.267   0.311  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.406   1.148  -1.290  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.256  -0.261  -1.268  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.054  -2.336   0.234  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.408  -1.171   1.575  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.389  -1.905  -0.240  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.971   1.411  -0.742  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.455   2.112  -0.699  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.780   1.912   1.031  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.697   1.889  -0.017  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.329   1.049   1.508  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9    9   21
CONECT   10   11   22   23
CONECT   11   24   25
END
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SMILES for HMDB0003647 (Perillyl aldehyde)

[H]C(=O)C1=CCC(CC1)C(C)=C
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INCHI for HMDB0003647 (Perillyl aldehyde)

InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-(1-Methylethenyl)-1-cyclohexene1-carboxyaldehydeChEBI
p-Mentha-1,8-dien-7-alChEBI
PerillalChEBI
PerillaldehydeChEBI
Perillic aldehydeChEBI
PerillylaldehydeChEBI
(-)-PerillaldehydeHMDB
1,8-P-Menthadien-7-alHMDB
1-PerillaldehydeHMDB
4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehydeHMDB
4-Isopropenylcyclohex-1-enecarbaldehydeHMDB
Dihydrocuminyl aldehydeHMDB
DL-Perillaldehyde(for perfumery)HMDB
FEMA no. 3557HMDB
L-PerillaldehydeHMDB
P-Mentha-1,8-dien-7-al (natural)HMDB
Para-mentha-1,8-dien-7-alHMDB
Perilla aldehydeHMDB, MeSH
4-Mentha-1,8-dien-7-alMeSH, HMDB
Perillaldehyde, (+)-isomerMeSH, HMDB
Chemical FormulaC10H14O
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
IUPAC Name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
Traditional Name(+)-perillaldehyde
CAS Registry Number2111-75-3
SMILES
[H]C(=O)C1=CCC(CC1)C(C)=C
InChI Identifier
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3
InChI KeyRUMOYJJNUMEFDD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point238.00 to 240.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility160.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.546Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP2.97ALOGPS
logP2.25ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability17.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.3931661259
DarkChem[M-H]-129.35131661259
DeepCCS[M+H]+137.27630932474
DeepCCS[M-H]-134.6530932474
DeepCCS[M-2H]-170.54830932474
DeepCCS[M+Na]+145.46630932474
AllCCS[M+H]+132.932859911
AllCCS[M+H-H2O]+128.432859911
AllCCS[M+NH4]+137.132859911
AllCCS[M+Na]+138.332859911
AllCCS[M-H]-135.832859911
AllCCS[M+Na-2H]-137.332859911
AllCCS[M+HCOO]-139.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.66 minutes32390414
Predicted by Siyang on May 30, 202216.3732 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.54 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2063.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid586.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid222.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid378.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid249.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid599.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid745.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)222.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1351.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid456.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1382.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid462.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid423.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate582.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA620.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water40.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Perillyl aldehyde[H]C(=O)C1=CCC(CC1)C(C)=C1862.0Standard polar33892256
Perillyl aldehyde[H]C(=O)C1=CCC(CC1)C(C)=C1241.5Standard non polar33892256
Perillyl aldehyde[H]C(=O)C1=CCC(CC1)C(C)=C1261.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized)splash10-005c-9700000000-a9b7244cc2e7179fa7062014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde EI-B (Non-derivatized)splash10-014i-9400000000-a85682020d5afcb60c382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde EI-B (Non-derivatized)splash10-016r-9200000000-489825eb61952c9dac222017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized)splash10-005c-9700000000-a9b7244cc2e7179fa7062017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9400000000-34a520c15ee51fc09bad2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl aldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-2d5f1aa73b10c86e86fd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 2V, positive-QTOFsplash10-0udi-0900000000-6a0c50ecfd39bc2355f12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 2V, positive-QTOFsplash10-0udi-1900000000-18ab37b64accb9eebc8a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 3V, positive-QTOFsplash10-0udi-1900000000-ff41ee428ac18fd924792020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 3V, positive-QTOFsplash10-0udi-2900000000-cc26f9d1f830b389dd6e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 3V, positive-QTOFsplash10-0udi-3900000000-b569eb4964b8859e157c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 4V, positive-QTOFsplash10-0ue9-3900000000-fc9bee20ab6457dc41d62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 5V, positive-QTOFsplash10-0zgl-6900000000-e4bd19c8534ad8a4170a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 6V, positive-QTOFsplash10-0kal-9800000000-7ae871e55ee7d93e3fd42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 8V, positive-QTOFsplash10-0a5c-9500000000-20075ac27a31f7c011ff2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 9V, positive-QTOFsplash10-0kyl-9300000000-606866a64c1614c828b52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 11V, positive-QTOFsplash10-00ou-9300000000-b59e349c4aa0f5f0f8b62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde Orbitrap 14V, positive-QTOFsplash10-00or-9200000000-20bc7958608312a537f32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-001i-2900000000-9efa35448eaa560e0b582020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-becd5fe890a229f54bb32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-001i-9000000000-faa2f39a1de11fcce3722020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-0a4i-4900000000-ff8554bb207ef1e442942020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl aldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-791c4364189bf936d4c32020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 10V, Positive-QTOFsplash10-0udi-1900000000-93f536e9e8fea0a3f4992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 20V, Positive-QTOFsplash10-0udi-5900000000-782526b3813e79dfb68f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 40V, Positive-QTOFsplash10-0uxu-9100000000-0dd1165ad555b037ef422016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 10V, Negative-QTOFsplash10-0002-0900000000-200f98d44579ee015dd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 20V, Negative-QTOFsplash10-0002-0900000000-bb22a8402cb0094ac0502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl aldehyde 40V, Negative-QTOFsplash10-0159-3900000000-fe4501ac4f2041d445922016-08-03Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014910
KNApSAcK IDC00003050
Chemspider ID15589
KEGG Compound IDC02576
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPerillaldehyde
METLIN IDNot Available
PubChem Compound16441
PDB IDNot Available
ChEBI ID15421
Food Biomarker OntologyNot Available
VMH IDPYLALD
MarkerDB IDNot Available
Good Scents IDrw1399441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

Enzyme Details
1. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Enzyme Details
2. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Enzyme Details
3. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
4. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
Enzyme Details
5. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
Enzyme Details
6. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails